Acetoxyacetyl chloride → N-[(1R,2S)-1-[4-(ethylsulfanylmethyl)phenyl]-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-propan-2-yl]-2-hydroxy-acetamide

HRID 1098797Notes

Reaction equation

HRID 1098797 reaction equation
Cl.[CH2:2]([S:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]([O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:21]=[CH:20]3)[C@@H:13]([NH2:15])[CH3:14])=[CH:8][CH:7]=1)[CH3:3].C([O:36][CH2:37][C:38](Cl)=[O:39])(=O)C>>[CH2:2]([S:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([C@@H:12]([O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[N:21]=[CH:20]3)[C@@H:13]([NH:15][C:37](=[O:36])[CH2:38][OH:39])[CH3:14])=[CH:10][CH:11]=1)[CH3:3]

Participants

3

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 66812805(1R,2S)-1-(4-(ethylthiomethyl)phenyl)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)propan-2-amine hydrochloride

Product 1

HCID 25013994N-[(1R,2S)-1-[4-(ethylsulfanylmethyl)phenyl]-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-propan-2-yl]-2-hydroxy-acetamide

Procedure

The title compound was prepared analogous to the method described in Example 21 starting from (1R,2S)-1-(4-(ethylthiomethyl)phenyl)-1-(1-(4-fluorophenyl)-1H-indazol-5-yloxy)propan-2-amine hydrochloride (25a) (50 mg, 0.11 mmol), and acetoxyacetyl chloride (13 μL, 0.12 mmol). Yield 33 mg (63%).

Sources & evidence

ORD record
ord-4fa50ce670f14bb8b07bb99a68887c0d
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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